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[ CAS No. 27425-92-9 ] {[proInfo.proName]}

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Chemical Structure| 27425-92-9
Chemical Structure| 27425-92-9
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Product Details of [ 27425-92-9 ]

CAS No. :27425-92-9 MDL No. :MFCD06797087
Formula : C21H44O11 Boiling Point : No data available
Linear Structure Formula :- InChI Key :YMBLPWKGRIGDBP-UHFFFAOYSA-N
M.W : 472.57 Pubchem ID :14550547
Synonyms :
Decaethylene glycol monomethyl ether
Chemical Name :2,5,8,11,14,17,20,23,26,29-Decaoxahentriacontan-31-ol

Safety of [ 27425-92-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 27425-92-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 27425-92-9 ]

[ 27425-92-9 ] Synthesis Path-Downstream   1~15

  • 1
  • <i>O</i>-benzenesulfonyl-<i>O</i>'-methyl-nonaaethylene glycol [ No CAS ]
  • sodium ethylene glycolate [ No CAS ]
  • [ 27425-92-9 ]
  • 2
  • [ 113694-55-6 ]
  • [ 112-60-7 ]
  • [ 27425-92-9 ]
YieldReaction ConditionsOperation in experiment
45% With potassium tert-butylate; calcium chloride; potassium t-butoxide (Aldrich, 95%, 39.0 g) was added to a solution of tetraethylene glycol (Aldrich, 412.7 g) and methyl hexaethylene glycol chloride from above (95.8 g) at 18 C. over a 25 min period (ice/acetone bath). The reaction mixture was then stirred at 120 C. overnight. The pH was adjusted to 7 by the addition of hydrochloric acid (12 N, 11.7 ml), and volatiles were removed (64 Pa (0.48 Torr), up to 185 C.). The residual dark oil was diluted with toluene (250 ml), and treated with calcium chloride (38.1 g). After stirring for 18 h, the mixture was filtered through Celite and concentrated to a dark oil (102 g), which was fractionally distilled to provide decaethylene glycol monomethyl ether as an amber oil (64.4 g, 45%). An analytical sample was obtained via chromatography on silica gel, eluding with 4% methanol in chloroform to provide a colorless oil; 1H-NMR (DMSO-d6) delta: 4.58 (t, J=5.5 Hz, 1, OH), 3.58-3.38 (m, 40, 20 OCH2), 3.24 (s, 3, OCH3). Anal. Calcd for C21H44O11: C, 53.37; H, 9.38. Found: C, 53.09; H, 9.47.
  • 3
  • [ 27425-92-9 ]
  • [ 177352-25-9 ]
  • 4-formylcinnamic acid decaethylene glycol monomethyl ether ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% titanium(IV)isopropoxide; at 110℃; for 18h;High vacuum; (c) 4-Formylcinnamic Acid Decaethylene Glycol Methyl Ether Ester A solution of methyl 4-(dimethoxymethyl)cinnamate (from step (b), 4.96 g), decaethylene glycol monomethyl ether (from step (a), 14.87 g), and titanium(IV) isopropoxide (Aldrich, 1.05 ml) was stirred at 110 C. under high vacuum for 18 h. The resulting black oil was then cooled to 35 C., treated with hydrochloric acid (1 N, 24.5 ml), and extracted with toluene (3*100 ml). The combined extracts were concentrated to a dark oil, which was chromatographed on silica gel. The title compound eluted with 10% methanol in chloroform as a yellow oil (4.60 g, 34%), 1H-NMR (DMSO-d6) delta: 10.54 (s, 1, CHO), 7.98 (m, 4, 4 phenyl CH), 7.76 (d, J=16 Hz, 1, CH=), 6.88 (d, J=16 Hz, 1, CH=), 4.31 (m, 2, CO2CH2), 3.70 (m, 2, OCH2), 3.51 (m, 36, 18 OCH2), 3.25 (s, 3, OCH3).
YieldReaction ConditionsOperation in experiment
Decaethylene glycol monomethyl ether (32). Monodispersed compound 32 was prepared from compound 31 and monodispersed triethylene glycol using the procedure described above in Example 17. Oil; Rf 0.41 (methanol: chloroform=6:10); MS m/z calc'd for C21H44O11472.29 (M++1), found 472.29.
  • 5
  • [ 477775-57-8 ]
  • [ 27425-92-9 ]
YieldReaction ConditionsOperation in experiment
Decaethylene glycol monomethyl ether (32). Monodispersed compound 32 was prepared from compound 31 and monodispersed triethylene glycol using the procedure described above in Example 17. Oil; Rf 0.41 (methanol:chloroform=6:10); MS m/z calc'd for C21H44O11 472.29 (M++1), found 472.29.
Decaethylene glycol monomethyl ether (32). Monodispersed compound 32 was prepared from compound 31 and monodispersed triethylene glycol using the procedure described herein. Oil; Rf 0.41 (methanol: chloroform=6:10); MS m/z calc'd for C21H44O11 472.29 (M++1), found 472.29.
Decaethylene glycol monomethyl ether (32). Monodispersed compound 32 was prepared from compound 31 and monodispersed triethylene glycol using the procedure described herein. Oil; Rf 0.41 (methanol:chloroform=6:10); MS m/z calc'd for C21H44O11 472.29 (M++1), found 472.29.
  • 6
  • [ 27425-92-9 ]
  • [ 11113-50-1 ]
  • [ 954142-69-9 ]
  • 7
  • [ 27425-92-9 ]
  • [ 109-92-2 ]
  • [ 1451212-92-2 ]
  • 8
  • [ 27425-92-9 ]
  • [ 2094-72-6 ]
  • C32H58O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; 1g of PEG monomethyl ester (PEG5000: 0.2mmol; PEG500: 2.1mmol) was dissolved in anhydrous DCM (PEG5000: 25ml; PEG500: 150ml) and cooled to 0C. Adamantane carbonyl chloride (5eq), DIPEA (10eq) and DMAP (1% cat.) were added and the mixture warmed to room temperature and stirred overnight under nitrogen. The mixture was transferred to a separating funnel and washed with 5% citric acid (50ml), saturated NaHCO3 (50ml), and brine (50ml). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. Ad-PEG500 was purified by column chromatography over silica gel (DCM/MeOH: 9/1) to yield the product E as a yellow oil (1.1g, 83%). Ad-PEG5000 was dissolved in a minimum amount of DCM and precipitated from diethyl ether to yield the product F as a white solid (805mg, 78%).
  • 9
  • [ 27425-92-9 ]
  • C21H43ClO10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; thionyl chloride; at 20℃; for 24h; A polyethylene glycol monomethyl ether (10) compound (manufactured by Zhongshan Chemical Co., Ltd.) and toluene were placed in a four-necked flask equipped with a condenser and a water separator, and heated under reflux to remove the polyethylene glycol monomethyl ether (10) compound. Moisture in the water.The polyethylene glycol monomethyl ether (10) compound was isolated by rotary evaporation. A water-removed polyethylene glycol monomethyl ether (10) compound (0.01 mol, 4.72 g) and pyridine 20 ml were added to a round bottom flask, and then thionyl chloride (0.03 mol) was slowly added dropwise with stirring at room temperature. 3.57g), After completion of the dropwise addition, stirring was continued at room temperature for 24 hours, and washing with diethyl ether three times to obtain a product of chloropolyethylene glycol monomethyl ether (10) having a structural formula of CMPEG-1 as shown above.
  • 10
  • [ 258516-82-4 ]
  • [ 27425-92-9 ]
  • C34H62O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% General procedure: (Using the synthesis of acetal 1a as an example). Under the atmosphere of N2, to a suspension of NaH (645 mg, 60% dispersed in mineral oil, 16.2 mmol) in THF (30 mL) at 0 oC was slowly added a solution of M-PEG 5 (1.1 g, 9.0 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt. The mixture was stirred for 30 min and a solution of chloromethyl aryl ether 13 (3.1 g, 13.5 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, the solution was concentrated under vacuum and the residue was purified by column chromatography on silica gel (CH2Cl2/MeOH = 50/1) to give acetal 1a as clear oil (1.2 g, 44% yield, 99.9% pure (HPLC), Fig. S2).
  • 13
  • [ 23601-40-3 ]
  • 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide [ No CAS ]
  • [ 27425-92-9 ]
YieldReaction ConditionsOperation in experiment
86% General procedure: (Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N2, to a suspension of NaH (1.0 g, 60% dispersed in mineral oil, 25.0 mmol) in THF (60 mL) at 0 was added a solution of M-PEG 5 (2.0 g, 16.6 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 8 (5.1 g, 20.0 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.6 mL, 33.3 mmol) and H2SO4 (0.4 mL, 8.4 mmol) were added to the reaction mixture and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give M-OEG 7 as clear oil (4.3 g, 88% yield).
85% General procedure: (Using the synthesis of 7e as an example). Under the atmosphere of N2, to a suspension of NaH (750 mg, 60% dispersed in mineral oil, 18.72 mmol, in 60 mL THF) at 0 C was added a solution of monomethoxy M-PEG 7b (1.50 g, 12.48 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 6a (4.80 g, 18.72 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.45 mL, 24.96 mmol) and H2SO4 (0.66 mL, 12.48 mmol) were added and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give monomethoxy M-PEG 7e as clear oil (3.04 g, 82% yield).
  • 14
  • [ 27425-92-9 ]
  • [ 530-62-1 ]
  • C25H46N2O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In dichloromethane; at 20℃; General procedure: (Using the synthesis of 1H-imidazole-1-carboxylate 14 as an example). To a solution of 1, 1'-Carbonyldiimidazole (CDI, 2.0 g, 16.6 mmol) in CH2Cl2 (40 mL) was added a solution of M-PEG 5 (1.0 g, 8.3 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred overnight at rt, and concentrated under vacuum, the residue was purified by column chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give 1H-imidazole-1-carboxylate 14 as clear oil (1.3 g, 71% yield).
  • 15
  • [ 5292-43-3 ]
  • [ 27425-92-9 ]
  • C27H54O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% General procedure: (Using the synthesis of tert-butyl ester 20 as an example). To a solution of M-PEG 5 (2.0 g, 16.7 mmol) in tert-butanol (80 mL) at rt was added potassium tert-butoxide (2.2 g, 20.0 mmol). The resulting mixture was stirred for 2 h at rt, followed by the addition of tert-butyl bromoacetate (6.5 g, 33.3 mmol). The resulting mixture was stirred for 12 h at rt and then filtered through celite. The solvent was removed under reduced pressure, the residue was purified by column chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give tert-butyl ester 20 as clear oil (2.4 g, 62% yield).
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